I think what trips people up more than anything isn't the way they dress, but the attitude they project. I took a valet with me on a job (unrelated to where they worked,) and the guy commented I had a demeanor that said, "I belong here," which he felt made me hard to spot... as it turned out, through further conversation, I had given his station bad marks before we met (though not him personally, I remembered him.)
I'm pretty sure that as long as you don't do anything to give yourself away and you dress at least semi-appropriately, the staff fills in the blanks as far as assuming how your lifestyle fits your clothing. Hotel staff have to deal with all kinds of loons, especially at nice hotels. Somebody will park their Ferrari in the valet zone and take the keys because they had an arrangement with a previous manager, or some 40-year-old regular will ask the staff to film him doing parkour.
That's it. I'm pretty sure it's 75% "I belong here." Your clothing can go up or down a few notches, though personally I usually go for something upscale but casual, something that doesn't really make an impression.